What Three Years of Trying Things Taught Me About Entrepreneurship

Three years ago, I walked away from my career without a clear plan for what would come next.

I was burned out, turning 40, and questioning what I wanted the next chapter of my life to look like. I’d spent nearly 20 years working in human-centered design, research, strategy, and customer experience. I knew how to understand people, solve problems, and help organizations make things better. But I wasn’t sure I wanted to keep doing that in the same environment.

I wanted more freedom to think outside the box, experiment, and build things. I wanted to work on things that felt meaningful, with people who cared about more than just the bottom line. And I wanted to explore some of the ideas I’d been thinking about for years but had never given myself the time to pursue.

So I did.

I explored hospitality and Airbnb design. I started a small business selling products from artisans in Ecuador. I returned to consulting, worked on websites and other projects, got my real estate license, and started working on deals. Eventually, while trying to solve a problem in real estate, I accidentally found myself building software with AI.

None of these experiences followed a plan. Each started with something I was curious about, an idea I wanted to explore, or a problem I thought I could solve.

Some gained traction. Some taught me what it takes to run a business. And some helped me realize that enjoying something and wanting to make it your full-time job are two very different things.

For a while, I thought the goal was to find the right business. If I could just find the right idea, I could build something successful, make a good living, and enjoy the work.

But the more I tried, the more I realized that the business idea itself wasn’t the whole answer.

I had to understand what I actually enjoyed doing, what I was good at, and what I wanted my days to look like.

I liked creating something from nothing. I liked understanding a problem, spotting opportunities, figuring out what people needed, and imagining how things could work better. I liked turning ideas into something tangible.

What I didn’t always enjoy was everything that came afterward: selling, constantly finding customers, managing operations, and maintaining a business indefinitely.

That didn’t make the businesses bad ideas, and it didn’t mean the experiments were failures. It meant I was learning something about myself that I couldn’t have learned by sitting around thinking about what kind of business I might want to start.

I had to try.

And trying taught me more than I expected.

I learned that I can enter an unfamiliar industry and figure things out. I learned that I can take an idea and get it off the ground. I learned that I don’t need to be an expert in every aspect of a business to get started.

I also learned that being capable of something doesn’t mean I want to do it every day.

Perhaps most importantly, I learned that I don’t have to turn every interest into a permanent business. Sometimes the value is in exploring the possibility, gaining experience, and discovering what you want to take with you into whatever comes next.

I don’t regret leaving corporate. There were certainly difficult moments, and entrepreneurship wasn’t always as fun or lucrative as I’d imagined. But I gave myself the chance to try things I’d wondered about for years, and I’m glad I did.

I didn’t come away with one perfect business idea that solved everything.

I came away knowing myself a little better.

And somewhere along the way, I stumbled into something that brought together skills I’d spent nearly two decades developing with an entirely new way of building things.

That discovery deserves its own story.

Because sometimes you don’t find what you’re looking for by planning your next move. Sometimes you find it by being willing to try something you never expected to do.